Tobacco product

ABSTRACT

A tobacco product is described which includes a 3-(2hydroxycyclohexyl) propionic acid, delta lactone having the structure   D R A W I N G

United States Patent [72] Inventors [21 Appl. No. [22] Filed [45] Patented [73] Assignee [54] TOBACCO PRODUCT 3 Claims, No Drawings 52 us. c1 '131/17, 131/144, 131/15, 131/9 [51] Int. Cl A24b 15/04 [50] Field ofSearch 131/17,

[56] References Cited UNITED STATES PATENTS 2,766,147 10/1956 Rowland 1 1/17 3,217,716 11/1965 Robertsetal 3,342,186 9/1967 Cook .1

OTHER REFERENCES SHMUK, A.A. THE CHEMISTRY AND TECHNOLOGY OF TOBACCO, PISHCHEPROMIZDAT, MOSCOW (1953) VOL. III, p.551.

Primary Examiner-Samuel Koren Assistant Examiner- Dennis J. Donohue Attorney-Kane, Dalsimer, Kane, Sullivan and Kurucz ABSTRACT: A tobacco product is described which includes a 3-(2-hydroxycyc1ohexyl) propionic acid, delta lactone having the structure Small amounts of this lactone enhance the flavor and aroma of the tobacco and improve the organoleptic qualities of the tobacco smoke.

BACKGROUND OF THE INVENTION Many substances are known which when added to a tobacco product improve the flavor and aroma of the tobacco smoke. Many of these substances, as for example, menthol, are highly volatile and impart to the tobacco smoke a flavor and aroma generally characteristic of the substance added. Much time and effort are devoted by the tobacco industry to develop additives which, when applied to a tobacco product, enhance the natural flavor of the tobacco as well as improve the organoleptic qualities of the tobacco smoke.

BRIEF SUMMARY A tobacco flavorant has now been discovered which, when added to smoking tobacco, substantially enhances the natural flavor and aroma of the tobacco and improves the organoleptic qualities of the tobacco smoke.

An object of this invention therefore is to provide a flavorant for tobacco which will improve the tobaccos flavor and aroma, and the tobacco smoke s organo leptic qualities.

DESCRIPTION OF THE INVENTION In accordance with this invention, tobacco flavor is enhanced by the addition of a saturated lactone 3-(2-hydroxycyclohexyl) propionic acid, delta lactone having the chemical structure tion, the following example is given:

EXAMPLE A keto ester having the chemical structure is formed by reaction of cyclohexanone with methyl acrylate in a Michael condensation. A keto acid having the structure 0 ll -CH2CH2C 02H is formed from the aforesaid keto ester by saponification. A solution of 0.11 mole of the keto acid, 0.115 mole of sodium hydroxide and 0.05 mole of sodium borohydride in milliliters of methanol is stirred under a nitrogen atmosphere for 4 hoursat 0 C. This solution is then acidified, saturated with ammonium sulfate and thereafter extracted with ether. The

ethereal extract is then washed with an aqueous solution of sodium bicarbonate, dried and concentrated. Distillation separates 68 percent of the product which is identified as 3-(2- hydroxycyclohexyl) propionic acid, delta lactone. This lactone consists of approximately 60 percent of the trans isomer and 40 percent of the cis isomer.

The resulting 3-(2-hydroxycyclohexyl) propionic acid, delta lactone is dissolved in ethyl alcohol and sprayed on shredded and blended domestic tobacco in amounts of 0.005 percent of the lactone by weight of the tobacco. After the ethyl alcohol is evaporated from the treated tobacco, cigarettes are made having a standard cellulose acetate filter. A second quantity of shredded and blended tobacco is sprayed with the same relative quantity of ethyl alcohol. After the ethyl alcohol is evaporated from the tobacco, cigarettes are made having a standard cellulose acetate filter. These cigarettes are used as the control for testing purposes. When compared to the control cigarettes, the 3-(2-hydroxycyclohexyl) propionic acid, delta lactone-treated cigarettes show a distinct improvement in the tobaccos flavor and aroma and the tobacco smoke s organoleptic properties. Procedures for making the above noted lactone contemplated by this invention are described in Vol. 62, pages 283287 of the Journal of the American Chemical Society, and Vol. 27, pages 4141 to 4146 of the Journal of Organic Chemistry.

It should be understood that the term tobacco product. as used herein are products made from tobacco such, for example, as cigarettes (either filtered or unfiltered), pipe tobacco and cigars. The lactone flavor additive may also be added to reconstituted tobacco or tobacco substitutes. It is also evident that the lactone contemplated by this invention may be added not only to the tobacco or filter tip section of a tobacco product but also to the cigarette paper wrapper or seam paste employed on the cigarette paper, or to the packaging material for the tobacco product. It is advantageous, however, that the lactone additive be included in the blended and shredded tobacco prior to its formation into a tobacco product.

We claim:

lIA tobacco product having added thereto a small amount of a lactone having the chemical structure such amount being sufficient to enhance the flavor or aroma of the tobacco product.

2. A tobacco product in accordance with claim 1 wherein the lactone is present in amounts of about 0.0001 to 2.0 percent by weight of the tobacco.

3. A tobacco product in accordance with claim 2 wherein the lactone is present in amounts of about 0.0001 to 0.05 percent by weight of the tobacco. 

2. A tobacco product in accordance with claim 1 wherein the lactone is present in amounts of about 0.0001 to 2.0 percent by weight of the tobacco.
 3. A tobacco product in accordance with claim 2 wherein the lactone is present in amounts of about 0.0001 to 0.05 percent by weight of the tobacco. 